Losing the sense of being in the know about what's going on at the company is one of the most common concerns I hear regarding working remotely. Both at the managerial level and between coworkers. There's a real fear that staying remote for too long will eventually lead to nobody really knowing what's going on, and thus the organization will drift apart.

The dread of that question is often underpinned by an assumption that the solution might be an even more frequent barrage of video calls to replace the stand-ups, management-by-walking-around, and other in-office practices that at least had a human feel to them. And if there's one thing we've learned during this pandemic, it's that even people who like meetings don't like virtual meetings in the same quantity. A few, okay. All of them, all the time? No.

But the real answer is simpler than you might imagine. The way to know what people are working on is simply to... ask them! Automatically and all the time. So that's what we do at Basecamp with two key questions: What did you work on today? and What will you be working on this week?

We pose these questions using Basecamp's automatic check-ins feature, and make it a norm that people working in development roles answer the daily question at least a few times a week, and that they answer the weekly question every week. It's amazing how much illumination these two questions alone can provide. Distributing a broad sense of what's going on at a company.

Part of the benefit here is that reporting progress isn't just a relationship between an employee and their boss, or even an employee and their team. It's available to the whole company! Or at least, that's how it works at Basecamp. If you run a company of many hundreds of people, you'd probably have to split it up somewhat, but while a traditional stand-up meeting might communicate status to a handful of people, these automated questions can easily do so to fifty people or more. That's a fundamental change.

In addition to distributing a broad feeling of what's going on in the moment, these questions provide a personal record of  what you've been working on over the long term. It's easy to get so caught up in the daily tasks that you forget to zoom out and gauge whether you're actually making progress on that big picture you're intend to paint. I often look back through my own answers at the end of a cycle to help calibrate on that.

It also serves as an early warning system when someone is struggling and needs help. If the answers are weak, vague, or vanishing for a long time, it's an invitation to checkin with that person. When someone is stuck, it's often hard to explicitly ask for help, but when their answers make clear that progress isn't happening, it serves as an implicit way of saying the same.

Finally, it's an invitation for cross-team pollination. I see all the time someone mention something they're working on, only to have someone from another team respond in a comment that actually they were dealing with the same issue from a different angle, and here's how we can fix it together. Exactly the kind of serendipitous encounters that people new to remote work keep yearning for the physical water cooler for.

Asking people what they've worked on and what they intend to work on frequently and automatically gives the company a daily pulse of progress. That goes a long way to counteract the feelings of isolation and separation when working remotely. A force of gravity to oppose the drift that might otherwise set in.